US2373261A - Sulphur dye composition and method of manufacture - Google Patents
Sulphur dye composition and method of manufacture Download PDFInfo
- Publication number
- US2373261A US2373261A US423991A US42399141A US2373261A US 2373261 A US2373261 A US 2373261A US 423991 A US423991 A US 423991A US 42399141 A US42399141 A US 42399141A US 2373261 A US2373261 A US 2373261A
- Authority
- US
- United States
- Prior art keywords
- sulphur
- printing
- solution
- manufacture
- amines
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title description 19
- 239000005864 Sulphur Substances 0.000 title description 19
- 239000000203 mixture Substances 0.000 title description 11
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 title description 3
- 150000001412 amines Chemical group 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000003638 chemical reducing agent Substances 0.000 description 10
- 239000003513 alkali Substances 0.000 description 6
- 150000004763 sulfides Chemical class 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- GRWZHXKQBITJKP-UHFFFAOYSA-N dithionous acid Chemical class OS(=O)S(O)=O GRWZHXKQBITJKP-UHFFFAOYSA-N 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000009972 noncorrosive effect Effects 0.000 description 2
- PGYZAKRTYUHXRA-UHFFFAOYSA-N 2,10-dinitro-12h-[1,4]benzothiazino[3,2-b]phenothiazin-3-one Chemical compound S1C2=CC(=O)C([N+]([O-])=O)=CC2=NC2=C1C=C1SC3=CC=C([N+](=O)[O-])C=C3NC1=C2 PGYZAKRTYUHXRA-UHFFFAOYSA-N 0.000 description 1
- 241001313185 Colias hecla Species 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- -1 aliphatic amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/30—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using sulfur dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
Definitions
- sulphur type of dyestuff The use of sulphur dyes, generally speaking, has been limited heretofore in the printing art, as distinguished from dyeing, since they normally contain sulphides as reducing agents and these sulphides have a corrosive action on the metal printing plates or rolls.
- sulphides are sodium sulphide, sodium hydrosulphide and sodium disulphide.
- the deleterious efiects of these reducing agents have definitely limited commercial use to date of the sulphur dyes for printing of fabrics.
- a. sulphur dyestuil that is entirely (or. 8-37) V
- the printing composition of our invention may be employed in the usual way for printing of suitable for printing purposes in view of the fact that it does not require any sulphides or similar reducing agents.
- the amines function apparently as solvents or dispersing agents for the dyestuil and convert the latter into a state of extremely finesubdivision, at least of colloidal size and in some instances perhaps of molecular size.
- the solution may be prepared in either 'weakor concentrated form as desired. In a commercially advantageous form the solution is capable of being filtered.
- the moist press cake that is commonly produced in the manufacture of sulphur dyes: and it is not-necessary to dry the sulphur colors to the usual dry powder form.
- the moist dyestufl press cake is easily dissolved or dispersed in an alkaline solution of an ethyleneamine.
- a press cake of the sulphur colors such as for example, sulphur black, blue, green or yellow, or any other desired sulphur color, is dissolved in a, caustic or other suitable alkali solution of the amine.
- the mixture is advantageously heated to accelerate the desired solubilizing effect of the amine or amines on the sulphur colors; although, in certain cases no heat is required.
- the temperature may vary from about room temperature up to the boiling point of the solution. An example of the latter is about 110" C.
- the amines that/wehave found suitable for dispersing or dissolving the dyestuffs include the ethylene and polyethylene amines.
- Examples of such amines are: ethylenediamine; diethylenetrlamine; triethylenetetramine; tetraethylenepen- 'tamine; pentaethylenehexamine.
- These amines may be" classified as straight chain, aliphatic amines: including both primary and secondary amines.
- Suitable examples of the amines useful in our invention may be represented by the following formula:
- a liquid, sulphur dyestufls composition that is adaptable for printing and is substantially free Of corrosive, agents, comprising an aqueous, alkaline, solution or dispersion or sulphur dyestufl and an openchain, aliphatic amine having the following formula:
- a liquor sulphur dyestuils composition comprising a substantially non-corrosive, alkali solution or dispersion of unreduced sulphur dyestufl's substantially free 01 sulphide, sulphite, and hydrosulphite or other corrosive reducing agents, and an amine having the iollowing i'ormula:'
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Patented Apr. 10, 1945 SULPHUR DYE COMPOSITION OF MANUFACTURE AND. METHOD Ewen D. Robinson and John C. Boesch, In, Mount Holly, N. 0., assignors to Southern Dyestufl Corporation, a corporation of North Carolina No Drawing. Application December 22, 1941,
Serial No. 423,991
Claims.
sulphur type of dyestuff. The use of sulphur dyes, generally speaking, has been limited heretofore in the printing art, as distinguished from dyeing, since they normally contain sulphides as reducing agents and these sulphides have a corrosive action on the metal printing plates or rolls.
Common examples of such sulphides are sodium sulphide, sodium hydrosulphide and sodium disulphide. The deleterious efiects of these reducing agents have definitely limited commercial use to date of the sulphur dyes for printing of fabrics. In accordance with our present invention we have produced a. sulphur dyestuil that is entirely (or. 8-37) V The printing composition of our invention may be employed in the usual way for printing of suitable for printing purposes in view of the fact that it does not require any sulphides or similar reducing agents. We have discovered that a new while omitting the usual sulphide reducing agents Y and in fact all other reducing agents, if desired.
The amines function apparently as solvents or dispersing agents for the dyestuil and convert the latter into a state of extremely finesubdivision, at least of colloidal size and in some instances perhaps of molecular size. This produces a liquid printing composition in the form of a colloidal dispersion or true solution; which we shall refer to hereinafter as a solution. The solution may be prepared in either 'weakor concentrated form as desired. In a commercially advantageous form the solution is capable of being filtered.
We are aware thatamines generally have been proposed heretofore ifor replacing the alkali in dyeing and printing compositions intended for use on wool, which would be damaged by the alkali. However, these compositions still employ the reducing agents such'as sulphides and are objectionable for the reasons. given above. Furthermore, we have found in actual practice that show an appreciation of the feature inherent in our invention; that is, certain amines may be used in alkali solution in lieu of the usual reducing agents.
fabrics. This normally involves the mixing of the dyestufi solution with a suitable printing paste (which may contain starch, gum, or synthetic printing materials) that gives the dyestufl' proper viscosity for use on the printing machines.
In preparing the printing composition of our invention practical use may be made of the moist press cake that is commonly produced in the manufacture of sulphur dyes: and it is not-necessary to dry the sulphur colors to the usual dry powder form. The moist dyestufl press cake is easily dissolved or dispersed in an alkaline solution of an ethyleneamine. In the usual case a press cake of the sulphur colors, such as for example, sulphur black, blue, green or yellow, or any other desired sulphur color, is dissolved in a, caustic or other suitable alkali solution of the amine. The mixture is advantageously heated to accelerate the desired solubilizing effect of the amine or amines on the sulphur colors; although, in certain cases no heat is required. Generally speaking, the temperature may vary from about room temperature up to the boiling point of the solution. An example of the latter is about 110" C.
The amines that/wehave found suitable for dispersing or dissolving the dyestuffs include the ethylene and polyethylene amines. Examples of such amines are: ethylenediamine; diethylenetrlamine; triethylenetetramine; tetraethylenepen- 'tamine; pentaethylenehexamine. These amines may be" classified as straight chain, aliphatic amines: including both primary and secondary amines. Suitable examples of the amines useful in our invention may be represented by the following formula:
(oinonrimnmnn in which a:=a whole number from l to? i1=a number between '0 and 4 and always one less than 0:.
In our compositionany one of the above repreture of the polyethyleneamines comprising diethylenetriamine, triethylenetetramine and tetraethylenepentamine. These amines, in'a 25% solution, have a pH value of around 12, and the final amass: 3 ing a sulphur dyestul'l press cake with an alkali 8. A sulphur dyestuiis solutionwhich is free of and a straight chain amine having the following the usual corrosive sulphides, hydrosulphites and formula: sulphites or other corrosive reducing agents and (Cal-I4) :(N'HalflNHh which in place thereof contains in combination in which z=a whole number from 1 to 5, =a number between 0 and 4 and always one less than 1:, and heating to street a substantially uniform solution of the several components.
4. A liquid, sulphur dyestufls composition that is adaptable for printing and is substantially free Of corrosive, agents, comprising an aqueous, alkaline, solution or dispersion or sulphur dyestufl and an openchain, aliphatic amine having the following formula:
wimmmnmmm in which m=a whole number from 1 to 5 and y=a number between 0 and 4 and always one less than 1:.
5. A liquor sulphur dyestuils composition comprising a substantially non-corrosive, alkali solution or dispersion of unreduced sulphur dyestufl's substantially free 01 sulphide, sulphite, and hydrosulphite or other corrosive reducing agents, and an amine having the iollowing i'ormula:'
in which a:=s. whole number from i to 5 and y==a number between 0 and 4 and always one less than :c.
sulphide and hydrosulphite reducing with the sulphur dyestufis a substantial amount 01' an open-chain, aliphatic amine having the formula (Cal-I4) :(NHs) 2(NH) y in which x=a whole number from 1 to 5 and pentamine.
10. In the process 01' producing a non-corrosive, sulphur dyestuii adaptable for printing textiles and substantially free of reducing agents,
the step of finely dispersing the sulphur dyestulf in an alkaline solution of a straight chain, aliphatic amine having an ethylene group, the dispersed dyestuil being flltrableand useful in a printing composition;
- EWEN D. ROBINSON. JOHN C. BOESCH, Js.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US423991A US2373261A (en) | 1941-12-22 | 1941-12-22 | Sulphur dye composition and method of manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US423991A US2373261A (en) | 1941-12-22 | 1941-12-22 | Sulphur dye composition and method of manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2373261A true US2373261A (en) | 1945-04-10 |
Family
ID=23681023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US423991A Expired - Lifetime US2373261A (en) | 1941-12-22 | 1941-12-22 | Sulphur dye composition and method of manufacture |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2373261A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472052A (en) * | 1949-05-31 | Liquid sulfur dye composition | ||
| US4309178A (en) * | 1979-10-22 | 1982-01-05 | Cassella Aktiengesellschaft | Process for isolating sulphur dyestuffs from aqueous crude melts containing sodium polysulphide |
| CN105566949A (en) * | 2016-02-04 | 2016-05-11 | 浙江长征化工有限公司 | Environment-friendly preparation method of sulphur dye solution |
-
1941
- 1941-12-22 US US423991A patent/US2373261A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2472052A (en) * | 1949-05-31 | Liquid sulfur dye composition | ||
| US4309178A (en) * | 1979-10-22 | 1982-01-05 | Cassella Aktiengesellschaft | Process for isolating sulphur dyestuffs from aqueous crude melts containing sodium polysulphide |
| CN105566949A (en) * | 2016-02-04 | 2016-05-11 | 浙江长征化工有限公司 | Environment-friendly preparation method of sulphur dye solution |
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